Coating composition



ether acids per se or Patented Dec. 22, 1942 UNITED STATES PATENTOFFICE.)

. Rudolf Endres, Dessau RossIan, Germany; vested in the Allen PropertyCustodian No 'Drawlng. Application January 24, 1940, Se-

rial No. 315,319. In Germany May 23,1936

9 Claims.

This invention relates to an improved coating composition comprisingcellulose derivatives and tetrahydroiuriuryl esters oicertainmono-carboxylic acids, and is a continuation-in-part of my copendingapplication Ser. No. 143,757, filed November 20, 1937, nowPatent No.2,191,428.

It is an object of the instant invention to provide improved coatingcompositions and plastic masses in the nature of lacquer coatings,films,

and the like which are stable in use and possess a high degree ofelasticity and adhesiveness.

In accordance with this invention superior coating compositions andplastic masses having 2 acids, such as with the butyl ester of an etheracetic acid.

The esters of tetrahydroiurfuryl alcohol and its homologues discussedhereinbefore are highly viscous, almost solid materials and readilydissolve cellulose derivatives, imparting thereto excellent gelatinizingaction and a very good plasticity. Lacquers, films or plastic massesprepared with these esters have excellent stability against cellulosicbase, such as a cellulose ether or ester,

are provided when such masses incorporate as softening, gelatinizin'gand solubiiizingagents a tetrahydroiuriuryl ester of certainmono-carboxylic acids. The tetrahydroiurfuryl esters include not onlythose derived iromdotrahydroiuriuryl alcohol but also those derived fromits homologues, such as those derived from methyl tetrahydrofuriurylalcohol.

A preferred group of tetrahydroiurfuryl esters are derived from othersof acetic acid. The ethers of acetic acid may be aliphatic,cycloaliphatic or aryl ethers provided the radical which is Joined tothe acetyl radical through the ethereal oxygen atom contains at least 6carbon atoms. Ether mono-carboiwlic acids illustrative of those formingsuitable tetrahydroiuriuryl esters are: octyl oxy-acctic acid,cyclohexyl-oxy-acetic acid, phenoxy-acetic acid, cresoxy-acetic acid,octylphenoxy-acetic acid, naphthyl-oxy-acetic acid.

and the like. 0

In accordance with another embodiment of the invention, wherein thehydrocarbon group of at least 6 carbon atoms contains a cycloaliphaticradical, it is not necessary that this radical be joined to the carboxylcontaining group through an ethereal oxygen atom linkage, but it. may bedirectly joined thereto through a carbon to carhon linkage. Suchcompounds are, for instance, the various substituted and unsubstitutedcycloparaiiin carboxylic acids, especially the naphthenic carboxylicacids.

The esters. of the present invention may be prepared by known methodseither by reactions involving the carboxylic acid per se or theiresters. For instance, in preparing the tetrahydroiuriuryl esters ofether acetic acids, the ether-s are first formed by the reaction of thehalogenated acetic acid aromatic alcoholates. Then tetrahydroiuriurylalcohol or its homologues are reacted with the with esters oi the withaliphatic, cycloaliphatic or cold and heat. To suit particularrequirements, they may be used jointly with other organic materials,such as, natural or synthetic resins.

The tetrahydrofuriuryl esters of the etherv acetic acids represent thepreferred ether acids of the instant invention. It is to be understood,however, that esters of the ethers of other lower molecular aliphaticmonocarboxylic acids, such as those derived from proprionic or butyricacid, may be used.

The examples which follow hereinafter, in

which the parts are by weight, will serve to illus- -trate the practiceof the invention but are not to be considered as a limitation thereon.

Example 1 Twelve parts of acetyl cellulose of medium viscosity aredissolved in i8 partsjoi a solvent mixture consisting of 20 parts'ofacetone, 15 parts oi methyl alcohol, 15 parts of ethyl acetate, 25parts of lactic acid ethyl ester, 15 parts of benzol and 10 parts ofmethyl chloride. Then 12 parts of'the tetrahydroiurfuryl'ester ofcresoxy acetic acid, which is a water-clear fluid having a boil-. ingpoint of 190 to 200 C. at a pressure of 9 mm. of mercury, are stirredinto the previously prepared solution. The resulting composition is alacquer possessing a high degreeof elasticity which can be used to sreatadvantage as coatings in the aviation industry.

Example 2 I One hundred and eighty-dour parts of nitro-.

cellulose of low viscosity mixed with alcohol in the ratio of 2:1 aredissolved in a solvent mixture consisting oi 25 parts of butanol, 125parts oi butyl acetate of 100% purity, 50 parts of lactic acid ethylester, 200 parts of toluol and 100 parts oi. xylol. Then 80 parts oftetrahydroiurfuryl ester oi cresoxy acetic acid and parts oi linseed oilare blown into the solution. Final1y;60 parts 01 a pigment paste, forexample, cadmium red,

together with 15 parts of the tetrahydroiuriuryl ester of cre'soxyacetic acid ,are stirredinto the previously prepared solution until itforms a ho ether 66 moseneous mass. 'A red, thick lacquer oi.excellacticacid ethyl ester.

ing lacquer is obtained lent elasticity and adhesiveness is obtained.This lacquer is admirably suited for coating wood. metal, leather andother like materials.

Example 3 Example 4 Thirty parts of nitrocellulose of low viscositymixed with alcohol in the ratio oi! 2:1 are dissolved in a solventmixture consisting of 20 parts of acetone, 10 parts of methyl acetate,'15 parts of butyl acetate of 100% purity and 10 parts of Then 15 partsof the tetrahydrofurfuryl ester of naphthenyloxy acetic acid are stirredinto the previously prepared solution. elastic and adhesive coatings.

Example 5 Three parts of nitrocellulose of middle viscosity mixed withalcoholin the ratio of 2:1 are dissolved in asolvent mixture consistingof 6 parts of butyl acetate of 100% purity, 6-parts of hutanol, 8 partsof cyclohexyl acetate, 12 parts of toluol and 12 parts of Xylol. Then 3parts of tetrahydrofurfuryl ester of aphthenic acids (middle molecularweight 220) are stirred into the previously prepared solution. Animpregnatpossessing a high degree of elasticity.

It should be understood that the present invention is not limited 'tothe specific esters and compositions herein disclosed but that itextends to all equivalents which one skilled in the art would considerwithin the general purport of the instant disclosure as limited only bythe appended claims.

Iclaim: I

l. A composition of matter suitable for the production of stable plasticmasses, coating compositions and the like comprising a cellulosicaliphatic mono-carboxylic acid wherein the radical joined to saidaliphatic radical through the ethereal oxygen atom contains at least 6carbon atoms.

A lacquer is obtained giving excellent 2. A plastic mass comprisingacellulosic base selectedirom a member of the group consisting throughthe ethereal oxygen atom contains at least 6 carbon atoms. 1

3. A composition of matter suitable for the production of plastic.masses, coating compositions and the like comprising a cellulosic baseselected from a member of the group consisting of cellulose ethers'andesters and an ester of tetrahydrofurfuryl alcohol with cresoxy aceticacid.

4. A stable composition of matter for the production of plastic masses,coating compositions and the like containing a cellulosic base selectedfrom a member of thegroup consisting of cellulose ethers and esters anda tetrahydrofurfuryl ester of ether acetic acid wherein the etherradical joined to the acetic acid radical contains analiphaticvhydrocarbon chain of at least 6 carbon atoms.

5. A stable composition of matter for the production of plastic masses,coating compositions and the like containing a cellulosic base selectedfrom a member of the group consistingof cellulose ethers and esters anda tetrahydrofurfuryl ester of' ether acetic acid wherein the etherradical joined to the acetic acid radical contains an alicyclic chain ofat least 6 carbon atoms.

6. A stable composition of matter for the production of plastic masses,coating compositions and the like containing a cellulosic base selectedfrom a member of the group consisting of cellulose ethers and esters anda tetrahydrofurfuryl ester of octyl-oxy-acetic acid.

7. A stable composition of matter for the production of plastic masses,coatingicompositions and the like containing a cellulosic base selectedfrom a member of the group consisting of cellulose ethers and esters anda tetrahydrofurfuryl ester of cyclohexyl-oiiy-acetic acid.

8. A composition of matter having a cellulose acetate base andcontaining a tetrahydrofurfuryl alcohol ester of cresoxy acetic acid asa plasticizing agent. I

9. A composition of matter having a cellulosic base selected from amember of the group consisting of cellulose esters and ethers andcontaining as a plasticizing agent a tetrahydrofurfuryl ester of anether acetic acid wherein the ether radical joined to the acetic acidradical contains ,an aryl hydrocarbon radical of at least 6 carbonatoms.

BUDOLF ENDRES.

